Total synthesis of cis-sylvaticin

被引:27
作者
Brown, Lynda J. [1 ]
Spurr, Ian B. [1 ]
Kemp, Stephen C. [1 ]
Camp, Nicholas P. [2 ]
Gibson, Karl R. [3 ]
Brown, Richard C. D. [1 ]
机构
[1] Univ Southampton, Sch Chem, Southampton SO17 1BJ, Hants, England
[2] Erl Wood Manor, Lilly Res Ctr, Surrey GU20 6PH, England
[3] Pfizer Ltd, Sandwich CT13 9NJ, Kent, England
关键词
D O I
10.1021/ol800767e
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
An asymmetric total synthesis of (+)-cis-sylvaticin is described. Key steps include the use of permanganate-mediated oxidative cyclization of 1,5-dienes to synthesize the two major fragments 2 and 3 and a catalytically efficient tethered RCM to unite these THF-containing fragments. In addition, t-BuP4 base was found to reliably promote rapid alkylation of the butenolide precursor fragment 4.
引用
收藏
页码:2489 / 2492
页数:4
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